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American entertainer Chris Brown was refused entry to Canada on Tuesday evening for being criminally inadmissible. His problems stem from two very famous assault convictions in 2009 and 2014. It has also been rumoured that he had also previously been denied entry into Canada on two prior occasions for the exact same reason.

Whatever your opinion of Chris Brown as a person or his music, there is no doubt that this refusal is expensive. As a result of cancelling sold out shows in Montreal and Toronto, concert promoter LiveNation is refunding the tens of thousands of tickets purchased. Along with lost ticket and merchandising revenue, there are also enormous sunk non-recoverable expenses. These include rental of two of Canada’s largest concert venues; marketing; cost of having the crew ship, set up and break down a very elaborate stage, sound and lighting system; hotels; administrative costs etc. etc. etc. This will easily cost millions and all because one single issue was not properly dealt with upfront.

Given the amount of money at stake and the prior refusals, the most prudent way of proceeding would have been to seek a special permission from a Canadian visa office even prior to the scheduling of the concerts.

Although his management team did say on Twitter that they were “ready at their end”, at best this would appear to be saying that they were going to attempt to apply for this permission that day. Trying to make an application at a port of entry on the day of the concert was not particularly wise. Given Mr. Brown’s notoriety, nature of his offences and his very public continuing legal challenges, hoping to find a sympathetic ear with an official who would take the personal heat of granting this permission was pretty much doomed to failure. In this case, playing ‘Border Officer Roulette’ had the same nasty outcome as playing ‘Russian Roulette’.

Given the fact that he sold out two major shows, LiveNation may be willing to give it another go with Chris Brown. In a global market with international talent, this incident is a very expensive lesson that borders matter. Lets hope for their shareholder’s sake that they insist that some proper advice whenever the talent leaves their home country to do an event they are promoting.

To tell you the truth, I never heard of Roger Ver until a few weeks ago, when the Twitterverse blew up regarding his rejection for a US visa. This rejection was completely contrary to the experience I have had with my US expatriation clients going back 25 years. In all of that time, I had never had a client refused a US visa (if they needed one) or been so much as pulled over at a US port of entry, let alone denied entry. Had the US completely changed its long standing attitude towards expatriates overnight, or was there more to the story than what met the eye?

I started with hearing what Mr. Ver had to say. It was a story of persecution and government ineptness, but was it credible? A quick public search on the internet, and credit records was revealing. First, Mr. Ver was convicted of a serious crime in the US and served 10 months in jail. While, he brushes this off as “ persecution for his libertarian views”, a read of the publicly available court proceedings seems to make this a bit of a stretch. What is not at issue is the conviction and the sentence. Next according to credit information, since his release, it would appear that Mr. Ver has been living in California and Hawaii rather than Japan as he claimed. That would make sense, as the Japanese are very leery of letting even visitors in with criminal records, let alone issuing some type of residence status. While he apparently has been at least interviewed by journalists in Japan, it would be interesting to find out if he ever disclosed to the Japanese his criminal past. While he may be doing a bit of “resume expansion” for “street cred” regarding claiming living in Japan, its not criminal. However, it does undermine any claim he might have that he “tried to submit a bunch of proof he lived in Japan” to American officials who refused to accept it. It would also explain why he applied for a B1/B2 visa at the American visa office in Barbados (responsible for St. Kitts and Nevis) rather than Tokyo (which deals with legal residents of Japan).

With regards to the failed US B1/B2 application, Mr. Ver needed to prove to US officials that he had sufficient residential connections with a country within that office’s jurisdiction. This was to overcome INA s. 214(b) that he intended to immigrate to the US. Since he chose to apply at the US Embassy in Barbados, he would be required to satisfy US officials of his ties to a country within their jurisdiction such as the one of his adopted citizenship, St. Kitts and Nevis. Mr. Ver may have absolutely no ties to St. Kitts aside from citizenship, if he acquired his citizenship under the Sugar Fund donation path rather than by purchasing an eligible residence. He certainly didn’t mention a home in St. Kitts during his various radio interviews. Even if Mr. Ver had been able to show sufficient ties to St. Kitts to overcome the immigrant intent, then the B1/B2 visa could still have been denied under INA 101(h) as he had a prior serious conviction. It should be noted that those pundits who cite the Reed Amendment, barring US “tax” expatriates, are way off-base. The regulations required to enable this provision have never been passed. Therefore, it cannot not be used to bar an American expatriate from entering the US. In addition, Mr. Ver had no special RIGHT to a B1/B2 visa just because he was previously a US citizen or was and is still paying taxes to the US treasury. In short, with proper legal advice, he should have known that he would not have met the non-immigrant standard or overcome the criminal inadmissibility bar prior to renouncing his US citizenship.

It should also be noted that Mr. Ver has not yet appeared upon the list of US renunciations, despite having expatriated almost a year ago. It is noteworthy that this list only contains “Covered Expatriates” , who are individuals who renounce either their US citizenship or long-term resident alien status AND meet certain net worth or tax paid thresholds. This may be because he will be on a future list or like his claim to live in Japan, his claimed net worth or US tax bill is a bit inflated.

Now onto the question of his acquisition of St. Kitts citizenship. St. Kitts recently had their visa-free travel to Canada revoked as a result of an incident involving questionable judgement on the government’s part. This followed on the heels of a prior US Treasury warning about the St. Kitts citizenship program . As a result, St. Kitts decided to cancel all existing passports and make all citizens re-apply. It is worth noting that under international law, a passport is the property of the issuing government, not the actual citizen. This fact is printed on the inside cover of most country’s passports and is undisputed. As Mr. Ver renounced his US citizenship in early 2014, we can therefore reasonably surmise that his St. Kitts citizenship was issued prior to this date. Therefore, Mr. Ver will be in the unenviable position of asking the St. Kitts government to issue him a new passport. If they decide not to do this (or revoke one that was issued within the past few weeks), then despite the fact that he is a citizen, Mr. Ver may find himself without a passport that would allow him to travel. If he is in St. Kitts, then he would be stuck there. If he is abroad, then he will be in that country without a valid passport and therefore probably find himself deportable to St. Kitts.

The next question is whether St. Kitts could take steps to strip him of their citizenship because of his criminal past? Depending on the facts in the application, St. Kitts could seek to claim that there was a material misrepresentation on the citizenship application. The remedy they would seek would be to strip Mr. Ver of his citizenship. However, there might be an argument that since he has already renounced his US citizenship, such an act would render Mr. Ver stateless. There is a UN Agreement on Statelessness that was signed by the UK but not by the US. St. Kitts obtained independence from the UK in 1983, after the UK signed onto this Agreement. There could be an argument that they are also signatories and therefore are treaty blocked from revoking Mr. Ver’s citizenship as it would render him stateless as a result. This looks like years of litigation ahead.

In summary, I will leave it up to the court of public opinion as to whether Mr. Ver is a martyr. What is pretty clear is that if he got any advice through this whole process, it was not very good. Before spending any time or effort in seeking a second citizenship for the purposes of expatriation, Mr. Ver should have sought out proper US immigration advice as to if and how he could overcome a criminal inadmissibility bar. If this first hurdle could be cleared, he should have tried to acquire citizenship in a country which does not require him to obtain a US visa. If not possible, then he should have sought advice as to whether St. Kitts was the best option for him. If it did turn out to be the best choice he should have made sure that he not only acquired St. Kitts citizenship, but also supplied himself with a multitude of “indicia of residence” to be able to satisfy officials that he was not an “intending immigrant”. Since he apparently did none of this, my only advice to Mr. Ver at this point is to go house hunting in St. Kitts. He should also make sure that he has good internet service as it looks like he will be attending most future Bitcoin conventions by Skype either because he may not be issued a new passport or he may even have his St. Kitts citizenship revoked.

He may be the “Bit-coin Jesus” but he sure proved that “Penny-wise is Pound Foolish” when it comes to seeking proper legal advice on something as serious as a US expatriation.